Hiring is one of the hardest things in a startup. Those first hires are crucial to creating the company culture and reputation you want. While making sure you have the talent you need in any department can be challenging, ensuring you bring the right sales team on board could be make or break for your initial traction.

The sales team is there to bring your product to the world. As your first line of customer interaction, it’s incredibly important to ensure you have the right people championing your product – both for your revenue and reputation.

I’ve helped many startups optimise their hiring process, and these are the three biggest mistakes I see founders make when hiring their sales team.

1. Seeking the Wrong Salespeople

There are three types of salespeople you need to watch out for while hiring. They’ll all look appealing at first, but each of them can cause serious damage.

The Veteran

Here’s the hard truth: great salespeople aren’t looking for jobs. They’re too good to be unemployed, and an early-stage startup can’t offer enough value to attract an experienced, high-performing salesperson.

If you see “experienced” salespeople (or worse, sales executives) advertising on job boards, they’re probably more scam artist than salesperson. There’s only one thing these people are typically really great at selling: themselves to potential employers. When it seems too good to be true, it probably is.

The Wolf

The wolf is your typical high-pressure salesperson. They’re effective at closing deals, but terrible at building and maintaining relationships. Their deals almost always lead to buyer’s remorse, because they don’t properlyqualify their prospects.

These salespeople will hurt your reputation and cost you a fortune in onboarding and support fees when the majority of their accounts churn in a month or two.

The Lamb

The lamb is a soft sales specialist who everyone likes but no one respects. They don’t use influence, leverage, or power to their advantage. Instead, they offer their prospects a choice and let them make the decision by themselves.

The problem is that prospects need help—and oftentimes some nudging—making decisions. The easiest and safest thing from the prospect’s point of view is typically to postpone the decision or simply go with the safest bet. A great sales person will take charge of the conversation, and move the sale ahead.

The Ideal Salesperson

So if your startup doesn’t want veterans, wolves, or lambs, what type of salesperson should you hire? Start by identifying the core traits that you need in a salesperson. In our experience, that’s someone who is hyper-competitive and highly compassionate.

This salesperson doesn’t operate from hostile strength (like the wolf) or friendly weakness (like the lamb). Instead, they sell withfriendly strength. Like a good parent, they want what is best for the prospect and will stop at nothing to make sure they get it.

2. Asking the Wrong Questions

Some people do well in interviews because they’ve prepared answers to the most common interview questions, like:

“What interests you about this job?”

“Tell me about yourself.”

“How would you deal with [insert sales objection]?”

Those questions are valuable, but they don’t tell you anything about who your candidate really is. As an interviewer, it’s your job to uncover the person behind the answers. The best way to do that is by following up every canned answer they give you with one simple question: “Why?”

For example:

You: “How would you handle a prospect who told you that our product was outside their price range?“ Candidate: “That’s a great question. Let me tell you about… [insert rehearsed BS].” You: “That’s great! Why?” Candidate: “Because I really… [insert more BS]” You: “Interesting. And why do you think that is?” Candidate: “Oh, well…” (now their answers aren’t as polished and they’re forced to think instead of recite) “So, in the end… [probably still 50% BS]” You: “Okay, that’s good. Why?” Candidate: “Oh, uh, well, um…” (now they’re really outside of their comfort zone. They’re less articulate and more introspective) “Well, to be honest… [insert genuine answer that reveals who they are as a person]”.

Those are the insights you’re looking for. Until you move beyond their rehearsed answers, you can’t accurately judge if they’ll be a good fit. Keep pressing your candidates until you’re certain you’re talking to the “real” them.

3. Hiring Before Trial-ing

To illustrate, what’s the best way to find out if someone is a great basketball player?

Is it to: Ask them insightful questions and follow-up with, “Why?”, or just watch them play?

Some candidates are great in an interview and terrible in sales. The only way you can judge their performance is to watch them in action.

If someone seems like a good fit, ask them to get on the phone and start selling. If the candidate is really interested, they’ll be more than willing to close a deal for you. Listen in and track their performance. Even if they didn’t close the deal, did they handle themselves well? If so, onboard them!

In closing

Even with the right questions, candidates, and tests, hiring will never be an easy process. You’ll make mistakes and sometimes you’ll have to fire people.

In the end, it comes down to going with your gut. If you see something in someone, take a risk. If you give someone the chance to prove themselves, they’ll probably do it.

Still struggling to hire an effective sales team? Sign up for our free Startup Sales Success course where I share the 7 characteristics to look for in great sales people and more startup sales advice. Until then, happy hiring!

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